Originally Posted by Cb
Easier said than done.
No offense.... But I will give some candid advice. I have experience.
I have a brother that is similar. I helped him out early on. My other Brother helped him, My mother helped him. Help means Money. We all eventually cut-off him off when it became obvious that he was milking it. He eventually hit rock bottom. He has since picked himself up and is beginning to improve. He went through a religous conversion and seems sincere. He has become more financially reponsible. However, I still do not loan him money. If he were in a dire emergency, I would probably help... But that would be it and the help would be limited!
You MIL is enabling the behavior. Your BIL will take all he can. Then move on to new territory (if he can find it). Unless you see a real behaviorial change (like a religious conversion)... Chalk him us as a user. I am sure I do not have to tell you this... But do not lend or give him any money. He is probably just pis#$ng it away!
Your DW is probably torn. You can try to negotiate a rational/reasonable plan with her. Get agreement that you might be willing to help in a dire emergency. Like getting thrown out of the house and need a few $ to get on their feet. Absolutely no discretionary spending. It just reinforces the behavior.
As far as the BIL's Daughter goes... If you want to help her. Help her to find a part-time job. Or pay her for doing some work for you. Do not pay if she does not live up to her end of the bargain or does sloppy work. Maybe she will learn some responsibility. Unfortunately she was born to a dead-beat. She needs to learn as soon as possible that there is no free-ride. People get what they earn! You will be doing her a favor by reinforcing good behavior.